Growing up with “unique” home life, I didn’t get to know much of my extended family.  In fact, I’m still trying to track them down one by one through 23andMe.  All I really had to go on was that my dad’s side had a lot of Spanish blood, and I look Spanish.  New Year’s 2017 was when I began vacation planning for the summer, and Spain was on my mind.  After a little research, and I mean like 20 minutes of looking at flights, my mind was made up, and I was going to spend a few weeks in Spain over the summer.

Madrid is enjoyed the most from the ground, exploring your way through it’s narrow streets that always lead to some intriguing park, market, tapas bar or street performer.  Each night we’d leave our hotel to begin a new adventure in Madrid, and nine out of 10 times we’d walk through the Plaza Mayor.

– Emilio Estevez


Logistics and Excursion Planning

When I began planning this trip, I had no idea how much I’d fall in love with the culture, people, and surroundings.  Instead of leaving myself a lot of free time to mosey around, I scheduled daily events.  Some that lasted a few hours, some that were 8-9 hours. 

Looking back now, I’m glad to have explored so much, but I would’ve enjoyed more time walking around and get lost in the streets of Madrid.  Emilio Estevez set the tone perfectly… just walking down the street is a culturally immersive experience that is pretty damn EPIC!

When traveling internationally, I usually go for 10-15 days.  This trip was exactly two weeks, so packing light is essential as I really didn’t want to drag around five bags and hundreds of pounds of clothes/shoes.  I still ended up with about 60 pounds worth, but that’s pretty good considering how many outfits and shoes I brought. 

Between day tours, heat, night activities (shows, dinners, etc.), it was a minimum of two outfits daily.  Delicate clothes, soft layers of luxury, and items simple to roll up and steam when needed were my solution.  

TB TIP: When traveling out of the country, don’t pay to convert money at the airport or any tourist support facility. The fees are high, and you can do this right at your bank, usually for free. If they do charge, it’s next to nothing. Think ahead, and do this before you depart.

So now the planning process.  While some view this as a daunting task, trust me, it’s fun when you know the ins and outs.  Here’s how I navigate it:

  • Find a Marriott property that suits my desires for this trip (each of these wants must be checked yes):
    • Something nice in the City to walk about and soak in the area.
    • Onsite lounge with breakfast, free beverages throughout the day, etc., to reduce living spend.
    • High floor room to hear less street noise.
    • Stay on points is available (it usually is, but out of country can be tricky, and sometimes it’s not an options). Also, inquiring into any fees that apply to foreign travelers is a must; you’d be surprised what I’ve encountered when not asking that question.
  • Check American Airlines website for flights from SNA (preferable) or LAX to MAD (Madrid) on points:
    • It’s a long flight to Madrid, so First Class with a lay flat bed on a jumbo jet is imperative.
    • I’m coming back from Barcelona versus a simple round trip to MAD, so looking at those options was another element to take into consideration.  Luckily British Airways is a fantastic airline and long-term partner of American Airlines, and I was able to secure First Class on a jumbo jet coming home as well.
    • The flights from SNA to DFW, then non-stop to MAD on a new Boeing Dreamliner, were less on points than LAX directly to MAD; 180k points versus 205k points.  
    • That didn’t bother me though, since it’s a 10-minute drive to my favorite airport (SNA) versus a super early flight, traffic, and long drive to LAX.
    • Easing into the SNA Admirals Club Lounge’s travel experience is the perfect way to start a trip!
  • Excursions:
    • To Viator, I went with the goal of exploring Spain’s history and culture.
    • Madrid is synonymous with ham, wine, Flamenco dancers, and bullfighting.  So, securing a little sampling of each over a couple of days was a must.  Okay, not bullfighting, but at least checking out the stadium and history.
    • Walking tours are always a win as you get to see new areas, learn the history, and get some great pointers from locals.  These are usually around 20-40 euros each, and I was able to secure one during lunchtime through Madrid’s older areas to sample food and wine.
    • Dinner and drinks (Sangria, of course) during a Flamenco show was around 75 euros, so I booked that as well.  Honestly, I was the most excited about this one.
    • There were some longer half-day excursions to very historical sites that intrigued me as well:
      • Avila to check out the Medieval City walls and castles.
      • Segovia to see the ancient aqueducts and castles.

Travel Day

When taking an international trip, I start my packing list about 30 days before ensure I can order anything I’ll need in time.  Packing itself begins about one week before travel so that the day of I can wake up stress-free, grab my bag and jump into an Uber. 

Get 8 hours of sleep; check!  Off to the airport at 7:30 to catch my 9 am flight; check!  TSA precheck straight to the Admirals Club Lounge for a coffee with Bailey’s; check!  It’s now onto my first flight from SNA to DFW, first class.  I really do enjoy an early flight in first class.  You get to board first, relax with a drink, and take a nap to make up for the early rise.  Although it wasn’t comfortable to sleep at first, given my excitement for the long flight and Spain, I eventually knocked out, waking up briefly for a fresh fruit breakfast inflight.  

Two hours later, I woke up to the wheels touching down in Dallas. Many people don’t care for DFW, given the size and tram between terminals.  Personally, it’s one of my favorites; large, clean, easy to navigate, and they have an American Express Centurion Lounge

If you have not experienced one yet, it’s a traveler’s MUST; admission is free with a Platinum or higher Amex card.  DFW’s lounge was Amex’s first. In my opinion, it is still their best location as they have spa services (15-minute neck & back massages for free, pedicures for purchase) and the best complimentary cuisine and signature cocktails.  After a massage and some nourishment, I was off to my gate.

Before boarding flight AA36, they announced that this was the maiden voyage for my Dreamliner, which meant I would be the first person to sleep in my lay flatbed (insert happy dance here)!  My first time on a Dreamliner was remarkable; these planes are like nonother and such a smooth flight.  In addition to fantastic food and service, I had 7 hours of peaceful and deep sleep that was uninterrupted by turbulence.

Landing in MAD was not what I expected.  I knew Spain was renowned for its architecture, but this airport took it to another level.  Getting through customs in a new country is always an experience.  There wasn’t a wait, and the agents were very kind. 

Each line had a soldier with an assault rifle in hand which was a little different, but I appreciate their dedication to safety.  MAD to the hotel was about 30 minutes.  Given that it was 10 am by the time I arrived at my hotel, my room wasn’t quite ready, so I took some time to document my trip and relax in the lounge.

Fast forward five hours, I was unpacked, showered, and napped.  Up and on the loose in search of a tapas and sangria experience, this was going to be an experience I’ll never forget.  What I didn’t take into account was the weather in Madrid being a little toasty in the summer.  It wasn’t unbearable; think 90 in the day and about 60% humidity. 

Okay, so after a 15-minute walk, I landed in a small restaurant that appeared to have just opened at 6 in the evening.  I was the only person there and had the bartender’s sole attention.  My Spanish is a little rusty, and his English still a work in progress; my order of sangria didn’t entirely yield what I had expected.  Enter TINTO DE VERANO, my new favorite drink (red wine and lemon Fanta) at around three euros throughout Madrid. 

Surprised this place had just opened, the bartender explained that people eat late in Madrid and that going to dinner before 10 pm was abnormal.  So no wonder my happy hour search at 3 pm was out of the ordinary.  Three plates of tapas and two tintos later, I cashed out for less than 20 euros and was on my way to further explore for a bit before a little cooling off at the hotel and some trip mapping, etc.  

Keeping in mind I’d be a lame tourist for trying to eat dinner before 10 pm, I located a highly rated restaurant on Yelp a few blocks from my hotel, made a reservation, and relaxed for a bit.  After all, I did just travel 6,000 miles and was in a very different climate, so more recharging never hurts. 

About dinner… this was the perfectly abnormal and hilarious way to end a travel day.  This restaurant was a neighborhood restaurant so-to-speak, I stood out like a sore thumb.  My Spanish came back to me enough, thankfully, as these guys didn’t get many tourists and did not speak much English nor care to.  The menu was very much local cuisine and kind of threw me for a welcomed loop; appetizers included squid, octopus, blood sausage, and a cheese plate. 

I never had blood sausage before, and surprisingly that was one of the multiple times while in Spain; rich but tasty.  Now for the main course, the daily special.  “Seabass” got lost in translation, and it turned out to be a traditionally prepared salt fish.  It couldn’t have been any funnier. 

The waiter was so proud bringing out a cart complete with onboard heating, a large cast-iron dish, the whole fish sizzling in oil which he promptly covered in scoops of sea salt and left it to “season” for a few minutes.  As if I didn’t stand out before, now I practically had a dunce hat on and every eye in the place gazing with amusement.  It was good, though!… and now it was time for bed.

Day One – Wine and Tapas 

My first full day in Madrid was pretty perfect.  I got a good night’s sleep and awoke to the subtle noises of a late-rising city starting to move.  Each city has its own unique vibe, so getting up and watching it come to life is a favorite to-do of mine when traveling. 

After a light breakfast and coffee, I reviewed my itinerary and started the day.  I only booked a two-hour tapas and wine tour today at 12:30 pm but figured it was the perfect way to get familiar with the culture and area.  After a short Uber ride, I was in the center of Santa Ana square (picture cobblestone, café’s, fountains, statues, and old buildings nicely adorned with modern touches), excited to meet my tour guide and get this experience started.

She was a wealth of knowledge this young lady, and I couldn’t have been more fortunate to have such a fun tour guide.  As we walked to our first destination, she shared the history of each building, street, and plaza, which really helps set the tone of the tour. 

First stop, wine!  We got a thorough education on the types of Spanish wine, the regions they come from, and the naming convention, which is all very different than American wines.  After finishing a glass Sincronia Negra, we were off to our next stop with a few history lessons along the way.  This time, we were sampling AND pairing wine with the perfect tapas.  

Several wines and little café’s later, I felt pretty educated on the local cuisine and dining trends.  Did you know that Jamon (cured pork/ham) carving is not only a dominant part of the cuisine in Spain but a sport, so-to-speak, with regards to competitions and rankings?  I didn’t before this tour, but it makes sense given the number of meat shops scattered around these little streets. 

On that note, strolling the streets of Madrid is magical!  The people were friendly and seemed laidback for the most part.  There were a lot of little shops that made popping into for a small dose of Spanish culture easy and entertaining.  With that in mind, I was heading back to my hotel and would find a good place for dinner that was nestled in the heart of Madrid’s late dining scene.  An 11 pm reservation in Santa Ana Plaza should round the day out nicely.

Day Two – Solo Madrid Exploration

To build on my first day, this was going to be a mellow one as well; only one thing planned, which was dinner and Flamenco performance at 8 pm.  After a little breakfast of fresh juices, coffee, fruits, meats, and cheeses, I spent some time mapping out Madrid. 

Primarily via Yelp and Google Maps to find highly rated and recommended spots, and then mapping out my route, of course.  The first stop was Plaza de Toros de Las Ventas (the bullfighting coliseum).  While I have zero interest in watching bullfights, it’s a several-century-old tradition in Spain, and I wanted to absorb some of the history.  But first, a 1-mile walk and some late brunch; Tinto de Verano and tapas.  

Las Ventas was what you’d expect from a coliseum-type venue built in the early 1920s and more!  The massive brick structure was beyond impressive regarding the construction quality and attention to detail, which seems to be a theme in Spain.  At the time, they weren’t giving tours, so I moseyed around on my own, got what I wanted, and hailed an Uber to the other side of town.  I was on my way to check out the Royal Palace and surrounding parks, botanical gardens, etc. 

Talk about amazing… acres and acres of greenery, stone, and finely manicured botanicals/grass/trees.  You’d think of the 2,000 rooms the Palace has they could’ve made one up for me, but nope!  Some walking, some nature, some pictures, and maybe one more stop for a Tinto, then my exploration would be done for the day.  After all, it’s hot outside, and I needed to rest and freshen up before dinner and the show tonight.

After a nap and shower, the only thing remaining of my day’s vibe was pure excitement for the Flamenco show.  Although I anticipated calling an Uber, they actually picked me up in a private van which was a pleasant surprise and saved me about 20 euros. 

The venue itself was definitely nostalgic; the wood had that classic smell, and it was adorned in traditional Spanish architecture and decorations.  I’ve found with all-inclusive excursions like this (meal and tour or show included), they are hit or miss.  This one was good, thankfully! 

The sangria was tasty, the food was cooked accordingly, but more important the Flamenco dancers were terrific.  Their energy and passion were unrivaled to any dancing I’ve previously seen.  I’d compare it to Broadway plays or the Opera in that it may not be something some people would do again, but it’s a once-in-a-lifetime experience, and you MUST take those when traveling.  After all, life is short, and it may be your last time in that City, Country, etc.

With a heart full of gratitude for this fantastic trip on points, the only thing left to do was make a stop at Plaza Mayor for a nightcap.  This is Madrid’s central plaza for nightlife and one that I could not miss while in town.  At 11:30 pm on a weeknight, it was BUZZING with people and energy. 

It still amazes me how differently the people of Madrid live, so carefree and full of energy to congregate and have fun daily.  Attributes I could admire and hope to absorb more while on this trip.  I could go on forever about my night, but this is a blog, after all, and not a novel.  So, after some sangria and people watching, I made my way back to the hotel to sleep and be prepared for an all-day tour the following day.

Day Three – Avila & Segovia

This tour is one of those you want to do since it maximizes your time and destinations visited, but given the 8-hour duration, it requires an early start time (8 am) which means you’re up early on vacation.  The bus stop was about 20 minutes away via Uber, so I left my hotel by 7 am to make sure I was early. 

A bit of advice from someone who has done it, don’t be late for your excursions.  They usually will not wait, and truly it’s just heartbreaking and frustrating to miss one.  Plus, you don’t get a refund for being late… Luckily I had a 1.5-hour drive on the tour bus to the first destination to get a good nap in.

The first stop was Avila.  A small province relatively high above sea level, this place has a lot of history, starting with its Medieval style wall surrounding the entire town.  It’s nearly 1,000 years old now and still standing strong, which is quite a sight to see. 

The city is not very large, but, has more churches and religious influence than most places I’ve traveled to that are much larger.  All in all, it’s an architectural masterpiece when you take into consideration how long ago most of the infrastructure was built and what it endured over the years.  I’m glad to have toured it with audio (something I always recommend even if you only keep one earbud in).

Next was on to Segovia and our lunch break, which was included in the tour; I know, taking a big gamble with two all-inclusive excursions back-to-back.  Fortunately, we ate first.  The tour of Avila was great, but it was a lot of walking in the heat, and I worked up an appetite. 

Segovia is an exciting place in that it’s equally old infrastructure-wise to Avila and incredibly nostalgic in that “what if I lived 500 years ago” way.  Lunch was quite hilarious, and to spare you a three-page breakdown, breakdown, let’s just say it was an ancient type of lunch that started with giant fava bean soup.  Okay, so lunch is done, and me now being one for two on the all-inclusive (it wasn’t that bad), time to tour the town. 

The aqueduct is the highlight here.  Having been built nearly 2,000 years ago, the fact that it’s still standing is impressive, and the fact that it’s still functional is astounding.  The Romans didn’t get it all right, but they sure did well with the architecture. 

After a thorough tour in-town, we ventured a little further out to the primary castle, which was equally impressive from a build and architecture standpoint.  From the top floor deck, which was used for entertaining, the views were amazing, and I took my sweet time snapping pics and leveraging my new GoPro.  

After a long day of epic historical experiences, I was glad to be heading back to Madrid to close out this chapter of my trip and head to Monaco for some much-needed luxury and R&R.

Trip Summary/Recap

Given this was my first time and first, I couldn’t have asked for more thus far of two destinations in Spain.  The history, the cultural experiences, and the brush up on my Spanish were all so perfect.  I could, and will, go back again.  And for me, that says a lot about how much I enjoyed the trip as a whole. 

If you’re going to make Spain a vacation spot, I recommend at least a week in-country. I planned nine days in total, 4.5 in Madrid and 4.5 in Barcelona (my next blog to be released), and could still have used more time.  It just means I have a reason to go back live a little longer in such a beautiful country.  

Tips & Tricks


  • Monitor the weather for the time of year you are traveling to Spain.  It can be quite warm or quite chilly based on the season.
  • Pool attire.  Yes, you will need it, and yes, Madrid is warm in the summer; cooling off after walking through the cobblestone streets is therapeutic.
  • Dining attire is necessary all-day tour attire won’t do for dinner in such a culturally spirited place. Think flowy dresses, vibrant colors, and overall fun attire. 
  • Most of the areas you will want to dwell in are cobblestone-lined streets in Madrid, so while you want heels for dinner, you may want to bring wedges to avoid the awkward trip unless you aren’t walking in evening attire.


  • The weather is dry, and elevation is higher than most metropolitan areas within the U.S.  I recommend bringing a packet of Liquid I.V. for each day you’re in Madrid and Europe as a whole.
  • Bring cash, it’s a welcomed form of payment with street vendors and the several small shops throughout Spain.  In fact, they gave me a discount in most shops for using cash.
  • Research online your tourist and dining spots.  I recommend hovering around Plaza Santa Ana and Plaza Mayor.  There is an abundance of culture, history, shopping, dining, and people watching.

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